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Literature summary for 3.4.22.69 extracted from

  • Turlington, M.; Chun, A.; Tomar, S.; Eggler, A.; Grum-Tokars, V.; Jacobs, J.; Daniels, J.S.; Dawson, E.; Saldanha, A.; Chase, P.; Baez-Santos, Y.M.; Lindsley, C.W.; Hodder, P.; Mesecar, A.D.; Stauffer, S.R.
    Discovery of N-(benzo[1,2,3]triazol-1-yl)-N-(benzyl)acetamidophenyl carboxamides as severe acute respiratory syndrome coronavirus (SARS-CoV) 3CLpro inhibitors: identification of ML300 and noncovalent nanomolar inhibitors with an induced-fit binding (2013), Bioorg. Med. Chem. Lett., 23, 6172-6177.
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

Crystallization (Comment) Organism
SARS-CoV 3CLpro bound with an inhibitor ML300 analogue, X-ray structure determination and analysis Severe acute respiratory syndrome-related coronavirus

Inhibitors

Inhibitors Comment Organism Structure
(2E)-N-[2-[4-(dimethylamino)butyl]phenyl]-3-phenylprop-2-enamide
-
Severe acute respiratory syndrome-related coronavirus
2-(1H-benzotriazol-1-yl)-N-(biphenyl-4-yl)-N-(thiophen-3-ylmethyl)acetamide
-
Severe acute respiratory syndrome-related coronavirus
2-(1H-benzotriazol-1-yl)-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]-N-[4-[(methylsulfonyl)amino]phenyl]acetamide
-
Severe acute respiratory syndrome-related coronavirus
2-(1H-benzotriazol-1-yl)-N-[4-(benzylamino)phenyl]-N-(thiophen-3-ylmethyl)acetamide
-
Severe acute respiratory syndrome-related coronavirus
2-(1H-benzotriazol-1-yl)-N-[4-(methylamino)phenyl]-N-(thiophen-3-ylmethyl)acetamide
-
Severe acute respiratory syndrome-related coronavirus
2-(1H-benzotriazol-1-yl)-N-[4-(pyridin-3-yl)phenyl]-N-(thiophen-3-ylmethyl)acetamide
-
Severe acute respiratory syndrome-related coronavirus
2-(1H-benzotriazol-1-yl)-N-[4-(pyridin-4-yl)phenyl]-N-(thiophen-3-ylmethyl)acetamide
-
Severe acute respiratory syndrome-related coronavirus
2-(5-bromopyridin-3-yl)-1-[5-(4-chlorophenyl)furan-2-yl]ethanone
-
Severe acute respiratory syndrome-related coronavirus
2-methylpropyl (4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)carbamate
-
Severe acute respiratory syndrome-related coronavirus
2-methylpropyl [4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]carbamate
-
Severe acute respiratory syndrome-related coronavirus
4-[(1H-benzotriazol-1-yloxy)carbonyl]-N,N-diethylaniline
-
Severe acute respiratory syndrome-related coronavirus
5-bromopyridin-3-yl thiophene-2-carboxylate
-
Severe acute respiratory syndrome-related coronavirus
5-chloropyridin-3-yl 1H-indole-4-carboxylate
-
Severe acute respiratory syndrome-related coronavirus
ML300 enzyme bound with a ML300 analogue highlights a unique induced-fit reorganization of the S2-S4 binding pockets leading to the first submicromolar non-covalent 3CLpro inhibitors retaining a single amide bond Severe acute respiratory syndrome-related coronavirus
additional information efforts to develop potent, non-covalent SARS-3CLpro inhibitors based upon a second chemical class of triazoles from our MLPCN screening campaign, detection of (benzo[1,2,3]triazol-1-yl)-N-(benzyl)acetamidophenyl carboxamides as enzyme inhibitors, noncovalent nanomolar inhibitors with an induced-fit binding, mechanism of action, overview. No inhibition by N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)benzamide, 2-methylpropyl (4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)carbamate, N-[4-(acetylamino)phenyl]-2-(1H-benzimidazol-1-yl)-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]acetamide, N-[4-(acetylamino)phenyl]-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]-2-(2-methyl-1H-benzimidazol-1-yl)acetamide, N-[4-(acetylamino)phenyl]-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]-2-(2-methyl-1H-imidazol-1-yl)acetamide, N-[4-(acetylamino)phenyl]-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]-2-(1H-1,2,3-triazol-1-yl)acetamide, and N-[4-(acetylamino)phenyl]-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]-2-[4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl]acetamide Severe acute respiratory syndrome-related coronavirus
N-(4-aminophenyl)-2-(1H-benzotriazol-1-yl)-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]acetamide
-
Severe acute respiratory syndrome-related coronavirus
N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)-1,2-oxazole-5-carboxamide
-
Severe acute respiratory syndrome-related coronavirus
N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)-2,2-dimethylpropanamide
-
Severe acute respiratory syndrome-related coronavirus
N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)-2-methylpropanamide
-
Severe acute respiratory syndrome-related coronavirus
N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)benzamide
-
Severe acute respiratory syndrome-related coronavirus
N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)cyclobutanecarboxamide
-
Severe acute respiratory syndrome-related coronavirus
N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)cyclohexanecarboxamide
-
Severe acute respiratory syndrome-related coronavirus
N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)cyclopropanecarboxamide
-
Severe acute respiratory syndrome-related coronavirus
N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)propanamide
-
Severe acute respiratory syndrome-related coronavirus
N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)thiophene-2-carboxamide
-
Severe acute respiratory syndrome-related coronavirus
N-[(1R)-2-(tert-butylamino)-2-oxo-1-(pyridin-3-yl)ethyl]-N-(4-tert-butylphenyl)furan-2-carboxamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-(2-acetylpyridin-3-yl)phenyl]-2-(1H-benzotriazol-1-yl)-N-(thiophen-3-ylmethyl)acetamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-(2-acetylpyrimidin-5-yl)phenyl]-2-(1H-benzotriazol-1-yl)-N-(thiophen-3-ylmethyl)acetamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-(acetylamino)phenyl]-2-(1H-benzimidazol-1-yl)-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]acetamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-(acetylamino)phenyl]-2-(1H-benzotriazol-1-yl)-N-[(1R)-2-[(2-methylbutan-2-yl)amino]-1-(1-methyl-1H-pyrrol-3-yl)-2-oxoethyl]acetamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-(acetylamino)phenyl]-2-(1H-benzotriazol-1-yl)-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]acetamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-(acetylamino)phenyl]-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]-2-(1H-1,2,3-triazol-1-yl)acetamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-(acetylamino)phenyl]-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]-2-(2-methyl-1H-benzimidazol-1-yl)acetamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-(acetylamino)phenyl]-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]-2-(2-methyl-1H-imidazol-1-yl)acetamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-(acetylamino)phenyl]-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]-2-(4-phenyl-1H-1,2,3-triazol-1-yl)acetamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-(acetylamino)phenyl]-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]-2-[4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl]acetamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]-2,2-dimethylpropanamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]-2-methylpropanamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]-3-methoxypropanamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]cyclobutanecarboxamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]cyclohexanecarboxamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]cyclopropanecarboxamide
-
Severe acute respiratory syndrome-related coronavirus
N-[4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]propanamide
-
Severe acute respiratory syndrome-related coronavirus

Organism

Organism UniProt Comment Textmining
Severe acute respiratory syndrome-related coronavirus
-
SARS-CoV
-

Synonyms

Synonyms Comment Organism
SARS-CoV 3CLpro
-
Severe acute respiratory syndrome-related coronavirus
severe acute respiratory syndrome coronavirus 3CLpro
-
Severe acute respiratory syndrome-related coronavirus

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0111
-
4-[(1H-benzotriazol-1-yloxy)carbonyl]-N,N-diethylaniline pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00003
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus 5-chloropyridin-3-yl 1H-indole-4-carboxylate
0.000051
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus 2-(1H-benzotriazol-1-yl)-N-(biphenyl-4-yl)-N-(thiophen-3-ylmethyl)acetamide
0.0005
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus 5-bromopyridin-3-yl thiophene-2-carboxylate
0.0007
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-[4-(2-acetylpyridin-3-yl)phenyl]-2-(1H-benzotriazol-1-yl)-N-(thiophen-3-ylmethyl)acetamide
0.00097
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus 2-(1H-benzotriazol-1-yl)-N-[4-(pyridin-3-yl)phenyl]-N-(thiophen-3-ylmethyl)acetamide
0.0015
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-[(1R)-2-(tert-butylamino)-2-oxo-1-(pyridin-3-yl)ethyl]-N-(4-tert-butylphenyl)furan-2-carboxamide
0.0015
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus 2-(1H-benzotriazol-1-yl)-N-[4-(benzylamino)phenyl]-N-(thiophen-3-ylmethyl)acetamide
0.002
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus 2-(1H-benzotriazol-1-yl)-N-[4-(pyridin-4-yl)phenyl]-N-(thiophen-3-ylmethyl)acetamide
0.0021
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus 2-(1H-benzotriazol-1-yl)-N-[4-(methylamino)phenyl]-N-(thiophen-3-ylmethyl)acetamide
0.0029
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-[4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]propanamide
0.0034
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-[4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]-3-methoxypropanamide
0.0036
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-[4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]-2-methylpropanamide
0.0038
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)cyclobutanecarboxamide
0.0041
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)-2-methylpropanamide
0.0041
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-[4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]cyclopropanecarboxamide
0.005
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus (2E)-N-[2-[4-(dimethylamino)butyl]phenyl]-3-phenylprop-2-enamide
0.0062
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-[4-(acetylamino)phenyl]-2-(1H-benzotriazol-1-yl)-N-[(1R)-2-[(2-methylbutan-2-yl)amino]-1-(1-methyl-1H-pyrrol-3-yl)-2-oxoethyl]acetamide
0.0069
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)propanamide
0.0077
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-[4-(acetylamino)phenyl]-2-(1H-benzotriazol-1-yl)-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]acetamide
0.0081
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-[4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]cyclobutanecarboxamide
0.0091
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)cyclopropanecarboxamide
0.0103
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus 2-methylpropyl [4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]carbamate
0.011
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-[4-(acetylamino)phenyl]-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]-2-(4-phenyl-1H-1,2,3-triazol-1-yl)acetamide
0.0125
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-[4-(2-acetylpyrimidin-5-yl)phenyl]-2-(1H-benzotriazol-1-yl)-N-(thiophen-3-ylmethyl)acetamide
0.013
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus 2-(5-bromopyridin-3-yl)-1-[5-(4-chlorophenyl)furan-2-yl]ethanone
0.0133
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-[4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]-2,2-dimethylpropanamide
0.02
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-(4-aminophenyl)-2-(1H-benzotriazol-1-yl)-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]acetamide
0.0221
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-[4-[(1H-benzotriazol-1-ylacetyl)(thiophen-3-ylmethyl)amino]phenyl]cyclohexanecarboxamide
0.0225
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)-2,2-dimethylpropanamide
0.0253
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus 2-(1H-benzotriazol-1-yl)-N-[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]-N-[4-[(methylsulfonyl)amino]phenyl]acetamide
0.026
-
pH and temperature not specified in the publication Severe acute respiratory syndrome-related coronavirus N-(4-[(1H-benzotriazol-1-ylacetyl)[2-(tert-butylamino)-2-oxo-1-(thiophen-3-yl)ethyl]amino]phenyl)-1,2-oxazole-5-carboxamide